Paying It Forward

I was 54 years old and had been divorced for fifteen years. During that time I had dated and had flings with a number of women and enjoyed new sexual experiences and levels of passion that were previously unknown to me. Were "pegging" or "snowball kisses" even a thing back in my single days? I am sure they were, and I'm also sure that my mindset at the time would have prevented me from partaking in those activities back then.

However, in my 50's I was a little more open to new sexual adventures and not only participated in those activities but enjoyed them as well. With the fond memories of being pegged and sharing cummy kisses, I had desires for more of the same.

However, with a slight twist, or maybe a kink, depending on your perspective. I figured the next step after being pegged and sharing cummy kisses with a female was to do the same with a t-girl. Sucking on a strapon was fun for a few minutes, but it made me curious about sucking on the real thing.

What could be better than a beautiful woman with a built-in real cock that she could fuck me with and also feed me a hot load of her lovejuice to share in a cummy kiss? Getting pegged by a female with her strapon and then having her kiss me with a mouthful of my cum after she blew me was hot and just what I fantasized about. Well at least it was right up until the moment I came in her mouth, and then my desire for the snowball kiss faded as quickly as my erection.

However, I figured my desire for a cummy kiss would not fade if the cum being shared was not my cum. I had already gotten down on my knees and sucked a woman's strapon cock and then spread my legs and let her peg me in various positions while I moaned in an unfamiliar voice like a happy hooker as her fake cock stimulated my prostate sending pleasure waves through my cock.

I assumed it would only be better to get down on my knees in front of a t-girl and suck her shecock and have her peg me, or to be more precise, fuck me. Mentally it was a big step to go from being pegged to being fucked, physically it was similar but far better to have the built-in tool instead of the strapon tool in my mouth and ass.

But there was one catch, the few t-girls I met up with either ejaculated too often or were on hormones and produced minimal to zero cum when they orgasmed. I expanded my search criteria by adding "passable crossdressers" figuring that no feminine hormones would result in more cum.

During my pursuit of a t-girl or CD who could fill my mouth with a load of hot cum, I came across an older gentleman who proposed an option that I had not yet considered, sucking a man's cock to get that elusive mouthful of hot cum. I politely declined his very generous offer as I told him that I was not interested in men. He countered that I was interested in cock and said, "I think that you are hiding you desire for cock behind a pair of panties."

He did make a good point, I did like playing with a cock and I wanted cum in my mouth, which aren't things a totally straight guy would desire, or at least admit to. But that was only the first part of my cummy kiss fantasy, sucking cock and getting a mouthful of hot cum.

The second part of my fantasy was to then kiss my lover with my mouthful of their cum, and I never imagined myself kissing a man. I was so convinced of it that I agreed to meet him at the local hot tub spa and show him in person that I wasn't interested in being with a man.

I would even venture to say that I was cocksure that I wasn't interested in being intimate with a man, right up until the moment he surprised me with a kiss and I surprised myself by kissing him right back. Then I went from cocksure to sure that I wanted to suck his cock.

I was very appreciative of him introducing me to the intense pleasures of m2m sex and intimacy and rewarded him with my passion, lust, and use of my body for his pleasure. And as he recognized, released, and revealed my sub site, his pleasure became my pleasure. He fucked my mouth and my ass and I kissed him with more passion and desire than I ever remembered kissing a female or t-girl.

He somehow recognized something about me that I hadn't recognized, or wanted to admit to, myself. From that moment on I decided I would pay it forward by someday introducing another man to the wonders of m2m sex and passion.

That's where this story really begins. I had been dog-sitting for a friend for the week and had been walking his dog through the neighborhoods where I used to walk with my sexy ex-girlfriend. One evening I passed by a house where oftentimes we saw an older couple working in their yard and we would offer greetings as we walked by. As I passed their house the husband was getting things out of his car and we waved to each other.

A couple of days later while I was walking the dog, he was in his front yard trimming the rosebushes by the sidewalk. Although we had seen each other many times in the past we had only acknowledged each other but had never spoken beyond casual greetings. He broke the ice and said, "I see you have a new companion for your walks." I told him that it wasn't my dog, that I was walking it for a friend.

He asked if it was my girlfriend's dog and I told him, "No, it's one of my friend's dog, my girlfriend and I broke up 6 months ago." He said he was sorry to hear that. I told him that I wasn't too sorry and that I didn't miss her, I only missed the sex. We both laughed and then he introduced himself, his name was Leo.

I introduced myself and asked how his wife was doing. He then informed me that his wife had passed away 10 months ago after a courageous battle with cancer. I offered my condolences and asked him how he was doing. He said things were getting a little bit better everyday but he still missed her. I think he was trying to lighten the now somber mood when he added with a chuckle, "And I miss the sex too!"

We made some more small talk before he said he better get back to the rosebushes while the sun was still up. I was about to continue on my walk when he said, "Hey, this was nice talking to someone for a change instead of moping around the empty house, would you like to swing by later to have a drink and talk some more?"

I told him that sounded like a great idea, my friend was coming by to pick up his dog at 7:30 and I could stop by at 8. He said, "Sounds good to me, it's a date, I mean, see you at 8."

Now I really didn't think he meant anything when he called it a "date" as I thought he was just making a rhyme and being friendly. I didn't get any vibe that he was interested in me or any man, I wondered if he picked up on the vibe that I was interested in him.

He was just the type of man who aroused my interest and more. He was about 10 years older, in decent shape,and came across more of a beta type than an Alpha type. For some reason I was attracted to men who were more beta in everyday life but tended to be Alpha in the bedroom. Perhaps it was because I was more Alpha in everyday life but recently discovered that I naturally gravitated toward being the beta male, the adoring sub, with another man.

It was 6 o'clock and I had two hours before I would meet Leo at his house. I must've tried on 10 different sets of clothes trying to look good for him. Since it was the summer I settled on a nice pair of shorts and a tight t-shirt. The only problem was that all of my nice underwear were in the hamper and I surely wasn't going to show up in my old tight-whiteys.

As I dug deeper through my underwear drawer I came across a pair of purple boyshorts that my ex-gf had left behind, probably because I hid them because they were perfect to jerk off in. I tried them on again and still liked the way they felt and looked so I decided to wear them. I didn't really expect that Leo would see them, but if he did it would definitely be an interesting topic of awkward conversation.

My friend returned from his vacation sooner than expected and picked up my furry new friend at 7. I now had an hour before I was to meet Leo. I jumped on my treadmill and ran hard for 5 minutes before I grabbed my barbells to do some arm and chest exercises. My mind was racing as I was pumping my body up physically and mentally for my "date" with Leo.

I had two goals for the night, have my tongue in Leo's mouth as we embrace in a passionate kiss, and have his cock in my mouth as I do my best to give him the best blow job of his life. The cummy kiss can come later, I wanted all of his hot sperm to myself tonight.

I laughed to myself thinking how much my life has changed since my older gentleman seducer boldly surprised me with my first m2m kiss. I thought about the hours that I spent lost in cock, drunk on cock, however you describe that indescribable feeling that all is right in the world when you have your lover's cock in your mouth and you know that sometime soon, but not too soon, a hot load of manjuice will be filling your hungry and horny mouth before you swallow his sperm to swim inside your beta male body.

And I thought about the times that I was wrapped up in my lover's arms as we kissed passionately, intimately, and sometimes even romantically. I had gone from never even thinking about kissing a man to thinking about it all the time and how magical it felt to bond with another man that way.

I might never have lived all those wonderful experiences and feelings were it not for that first bold kiss. That was what I wanted to pay forward, introducing another man to a new and heightened world of pleasure, passion, and incredible sex - with a man.

Of course, this wasn't a purely altruistic endeavor on my part. I already said what I wanted, his kisses and his cock. In the past after breakups I would get right back out there and find a new gf. And also in the past, after a few months I wished that I had stayed single, and instead of looking for a girlfriend I should have been looking for a t-girl girlfriend (should that be t-girlfriend?) or a male lover. You know, someone with a cock.

I decided to walk to his house to be more discreet than having my car parked in front of his house long into the night. At least that what I was hoping for. As I walked the few blocks to his house, I thought to myself that maybe this time I did it right and stayed single long enough to meet my perfect lover.

I arrived at his house casually late at 8:03, doing my best to not appear too eager. On my way over I thought about using the same tactic that my gentleman seducer successfully used on me. I'm not sure if he had planned it ahead of time to catch me off guard or if he just read the situation and went for it. But his perfectly executed strategy was to close the door behind me and greet me with a warm hug, then pull back from the hug, look me in the eye and go in for a quick peck on the lips, followed immediately by his tongue pushing into my mouth. That tactic obviously worked on me, but I didn't think it was the way to go with Leo.

He greeted me at the door with a firm handshake and confirmed my decision not go in for the quick close. He invited me in and offered a choice of cocktails. I told him I would have whatever he was drinking and make the first one a double. He smiled and said, "A man after my own heart."

I said, "You got that right" and to myself I thought "in addition to your kisses, cock, and cum". With drinks in hand he gave me a quick tour of his house and backyard, which was private and had an in-laws unit and a built-in hot tub off the patio. I noticed steam rising from the hot tub and immediately thought that could be a potential setting for my seduction plans. We stayed outside and sat on his patio enjoying our drinks and talking. The more I looked at him as we talked, the more I wanted to be his lover and him to be mine.

We finished our drinks and went back into the house to get refills. I stood maybe a little to close to him while he was mixing up new drinks but he didn't seem to mind or notice. He handed me my drink and I made a toast, "Here's to new friends" and we clinked glasses.

He looked me in the eye and said, "I would like that" and I responded "So would I" and smiled at him. God I wanted to put my drink down and hug him and kiss him at the moment but I didn't want to scare him off. Besides, he hadn't given me any signs that he was interested in or open to anything other than a new guy friend.

I thought maybe I could tell him that his hot tub reminded me of my first m2m encounter where I ended up sitting on my seducer's lap in the tub facing him and kissing him like a horny schoolboy. And when he sat on the edge of the tub I floated in the water while I sucked his cock, but instead it felt like I was floating in the air.

Nah, that might be too much to share too soon! Also, since that was part of my plan with him, I didn't want him to feel that it was scripted. I wanted him, my Leo, to feel special.

I decided I would lead the conversation about dating females and getting pegged, and gauge his reaction to determine if I should mention graduating to getting fucked by t-girls. And then see if I should, or needed to, go further and tell him about my experiences with men.

If going from getting pegged by females to getting fucked by t-girls was graduating, going from getting fucked by t-girls to getting fucked by men and sucking their cocks was getting my Master's degree in Bottom Studies. For me at least, t-girl cock was the gateway drug to male cock, and I became addicted.

We went back outside to the patio and sat down to enjoy our drinks and new friendship, but this time I sat kitty corner to him instead of across the table. I asked him how he was coping with the passing of his wife and he said he had recently come to accept it as she had been sick and in pain for a long time and she was now in a better place.

He told me his wife's caretaker had lived in the in-laws unit for the last 6 months of her life but it was empty now. I instinctively reached out and put my hand on his forearm and once again offered my condolences and said that things will get better every day.

He didn't pull back, he put his drink down and put his hand on mine and held it there for a while before he lifted his drink and said, "To better days ahead" and after we both took a swig I toasted, "And to better nights ahead". I was starting to think perhaps my plan would work and this was going to be the first of many better nights ahead.

I told him that after many years of dating and relationships, that I was taking a break from dating women. I wasn't sure if he would read anything into that, I was hoping he would. I went on to say that if he ever decides to start dating again, that women are a lot different than they were when he was single. He told me that he met his wife during Orientation in his Freshmen year in college and had never dated anyone else since then.

He asked me how women had changed and I told him they were more aggressive sexually, trimmed or shaved their pubic hair, enjoyed various sex toys, and best of all seemed more open to oral sex. He didn't flinch when I mentioned those things, he actually seemed quite intrigued and even mentioned that his wife was a good lover but wasn't overly enthusiastic about oral sex. That gave me hope that he would be open to a blow job, from me!

I then told him a partially true story, adapted to assist in my seduction, of a former female lover who insisted that I do everything in the bedroom that she did. He asked me, "So she wanted you to give her oral sex too?"

I just laughed and said, "I was already doing that, she meant she wanted me to taste my own cum and she wanted to fuck me as well."

That certainly got a reaction out of him as he said, "She sure sounds like a wild one, was she the one you used to walk by here with?" I told him that yes, she was the one and he said "And you said earlier today that you missed the sex with her."

He had me there, the only thing I could think of saying was, "Yes that's true, but I don't miss everything about having sex with her." That was actually a true statement, I was no longer interested in getting pegged by her strap-on or tasting my own cum in a snowball kiss, I wanted to get fucked by a real cock and taste someone else's cum. And at that moment, it was only Leo's cock, cum, and kisses that I wanted.

I continued on with my story and told him how my ex-gf once gave me an incredible blow job and after she finished she climbed up and surprised me by french kissing me with the mouthful of cum that I had just fed her. He seemed more interested than shocked so I added, "It was really sexy and made her so horny that once all the cum was gone she went back down for more!"

He looked at me with a smile and said, "You are one lucky guy." So I had just told him a story about having a cummy kiss that I thought was sexy and he thought I was a lucky guy, well just maybe I could get lucky with him.

I thought this would be a good segue to my story of getting pegged to see how far I could go before he flinched. I told him how after I accepted my first cummy kiss, it seemed to bring out my ex-gf's wild side. It started with a finger up my ass while she was sucking my cock, then two fingers, then the next weekend she used her slim vibrator.

I told him that I was a very weak man when she had my hard cock in her mouth and I would agree to just about anything at a certain point. And on top of that, it felt surprisingly good. He nodded and said, "The closest I've come to that is my annual prostate check, and it definitely is a unique feeling."

I wanted to see if he would share some more so I apologized for dominating the conversation with stories about my past exploits. He assured me that he was thoroughly enjoying both my stories and my perspective on the dating market. He asked me to continue and he heard how my ex-gf surprised me the following weekend by coming to bed naked, except for a harness with a 6" cock attached to it. She had shopped for a strapon that matched my cock as she thought it was only fair that I take what she takes.

Maybe for the first time in my life I was glad that I wasn't hung! I told her that I wasn't quite ready for that but she wasn't about to give up on her quest to peg me. She just reasoned that it wasn't any different from having her fingers or vibrator up my ass while she sucked my cock, that this way she could do it hands-free and could kiss me at the same time. I couldn't really argue with that logic, besides, I was more than a little curious to have her peg me with it.

She then went through her progression of one finger, two fingers, and then her slim vibrator up my ass all the while sucking my cock to perfection. When she had me moaning like a whore and begging to cum, she pulled out the vibrator and sat on the edge of the bed and demanded that I get on my knees between her legs. Once I was properly positioned she then said I had to suck her strap-on cock before she would fuck me and let me come.

Finally Leo flinched and asked, "Is that what caused you to break up with her?"

I laughed a little and said, "Remember that I told you I was a weak man when my cock was hard and I would agree to just about anything, well I was very weak at that moment and did exactly what she said."

He just nodded his head and said "Sound like you were stuck between a cock and a hard place." All I could do was laugh and touch his arm again.

I figured that was enough, if not too much information, on our first date. I really felt like I was on a first date, it didn't feel the same as hanging out with a new guy friend for the first time. I started to stretch my legs and arms as we sat there and he asked me if I was uncomfortable in my patio chair.

I told him I was very comfortable, my muscles were just a little stiff from working out earlier. We finished our second drink and headed inside for a refill. Once again I followed him closely like a lovesick puppy into the kitchen, being close to him made me feel so good.